Phenol → HCID 86596952, compound

HRID 2225254Notes

Reaction equation

HRID 2225254 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C@H:13]1[CH2:26][OH:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1(O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:14][C@H:13]1[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68765914tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate

Product 1

HCID 86596952HCID 86596952, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate (120 mg) in tetrahydrofuran (3 mL) was treated with phenol (45 mg) and triphenylphosphine (125 mg). The mixture was stirred at rt and treated dropwise over about 3 minutes with diethyl azodicarboxylate (74 μL). The mixture was stirred for 3.5 h, then was concentrated under vacuum. The residue was purified by flash chromatography on silica gel, eluting with 1:5 v/v ethyl acetate/hexane, to provide tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(phenoxymethyl)cyclohexylcarbamate as a white glassy foam (110 mg). MS found: (M+H)+=455.3.

Workup

  1. stirringThe mixture was stirred for 3.5 h
  2. concentrationwas concentrated under vacuum
  3. customThe residue was purified by flash chromatography on silica gel
  4. washeluting with 1:5 v/v ethyl acetate/hexane

Sources & evidence

ORD record
ord-3347ad9637fd46de9fc7efd07177271d
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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